A Compartmentalized‐type Bifunctional Magnetic Catalyst for One‐pot Aerobic Oxysulfonylation and Asymmetric Transfer Hydrogenation,ChemCatChem

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A Compartmentalized‐type Bifunctional Magnetic Catalyst for One‐pot Aerobic Oxysulfonylation and Asymmetric Transfer Hydrogenation
ChemCatChem ( IF 3.8 ) Pub Date : 2020-11-25 , DOI: 10.1002/cctc.202001553
Shitong Wang ₁ , Chengyi Wang ₁ , Ning Lv ₁ , Chunxia Tan ₁ , Tanyu Cheng ₁ , Guohua Liu ₁

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Utilization of the confined cavity of the mesoporous silica, the exploration of the synergetic catalysis process for sequential organic transformations has great significance in asymmetric catalysis. In this study, the yolk‐shell‐structured magnetic nanoparticles with the chiral Ru/diamine species within the nanochannels of the outer mesoporous silica shell and the FeCl₃ species on the inner magnet core are fabricated. The electron microscopy images and the structural characterizations disclose the uniformly distributed magnetic nanoparticles with the well‐defined single‐site ruthenium/diamine active centers onto the outer silica shell. As a yolk‐shell‐structured bifunctional magnet catalyst, the FeCl₃ species enables an efficient aerobic oxysulfonylation between aryl‐substituted terminal alkynes and sodium sulfinates to the β‐keto sulfones intermediates, and the ruthenium/diamine species sequentially reduces the in‐situ generated intermediate to the chiral β‐hydroxysulfones products. As we envision, this one‐pot aerobic oxysulfonylation/asymmetric transfer hydrogenation process affords various chiral β‐hydroxysulfones in high yields with excellent enantioselectivities. Furthermore, this magnetic catalyst can also be conveniently recovered via an additional outer magnet and repeatedly recycled, showing a potential application in industrial interest.

中文翻译：

隔室型双功能电磁催化剂用于一锅好氧羰基化和不对称转移加氢

利用中孔二氧化硅的密闭腔，探索有机相继的协同催化过程对不对称催化具有重要意义。在本研究中，制备了具有卵黄壳结构的磁性纳米颗粒，该纳米颗粒具有在外部介孔二氧化硅壳的纳米通道内的手性Ru /二胺物种和在内部磁芯上的FeCl ₃物种。电子显微镜图像和结构表征揭示了均匀分布的磁性纳米粒子，其具有明确定义的单中心钌/二胺活性中心在二氧化硅外壳上。FeCl ₃作为卵黄壳结构的双功能磁体催化剂物种使在芳基取代的末端炔烃和亚磺酸钠之间的有效好氧氧磺酰化成为β-酮砜中间体，而钌/二胺物种依次还原了手性β-羟基砜产物的原位生成中间体。正如我们所预想的那样，这种一锅式好氧氧磺酰化/不对称转移加氢工艺可提供高收率的多种手性β-羟基砜，具有出色的对映选择性。此外，该磁性催化剂还可以通过额外的外部磁体方便地回收并重复循环使用，在工业上具有潜在的应用前景。

更新日期：2020-11-25

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